TWI572614B - 可用於製造無鹵素阻燃性聚合物之含磷化合物 - Google Patents
可用於製造無鹵素阻燃性聚合物之含磷化合物 Download PDFInfo
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- TWI572614B TWI572614B TW101118525A TW101118525A TWI572614B TW I572614 B TWI572614 B TW I572614B TW 101118525 A TW101118525 A TW 101118525A TW 101118525 A TW101118525 A TW 101118525A TW I572614 B TWI572614 B TW I572614B
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- phosphorus
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- 229910052698 phosphorus Inorganic materials 0.000 title claims description 26
- 239000011574 phosphorus Substances 0.000 title claims description 24
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 title claims description 22
- 229920000642 polymer Polymers 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000003822 epoxy resin Substances 0.000 claims description 9
- 229920000647 polyepoxide Polymers 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002966 varnish Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 12
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- -1 phosphorus halide Chemical class 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/04—Epoxynovolacs
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/04—Epoxynovolacs
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Description
本申請案係請求於2011年5月25日申請,名稱為“可用於製造無鹵素阻燃性聚合物之含磷化合物"之美國臨時專利申請案第61/489,705號案之優先權,其教示內容在此併入本案以為參考資料,如同於下完整再現般。
本發明係含磷化合物;其作為聚合物(特別是環氧、聚胺甲酸酯、熱固性樹脂及熱塑性聚合物)的阻燃劑之用途;及此等含阻燃劑之聚合物製造保護性塗覆組成物及阻燃性製造物件(諸如,電層合物、聚胺甲酸酯發泡體,及各種模製及/或發泡熱塑性產物)之用途的領域。
阻燃性聚合物典型上係使用含鹵素之化合物以提供阻燃性。但是,於阻燃性聚合物市場係增加對無鹵素組成物之需求。與環氧樹脂具反應性之以磷為主之阻燃劑係正被商業化用於熱固性環氧樹脂組成物。但是,此阻燃劑需使用一多步驟方法製備,因此生產係相對較昂貴。再土,習知技藝所述之方法提供難以特性化之寡聚物混合物。
因此,仍需要提供一種與習知技藝所述之材料相比係可較不昂貴地被製備且可以高純度製造之反應性無鹵素阻燃劑。
一種用於製造含磷化合物之方法,包含:
將(A)與(B)接觸,由此所構成,或基本上由此所構成,
其中,RA及RB彼此獨立地係選自由經取代之芳基基團、經取代之芳氧基基團、未經取代之芳基基團、未經取代之芳氧基基團、經取代之烷基基團、經取代之烷氧基基團、未經取代之烷基基團,及未經取代之烷氧基基團所構成之族群;或其中,RA及RB被組合形成環狀結構;其中,RC係含有每分子為1至12個碳原子的範圍之一烴基基團,且係選自由甲基、乙基、異丙基、正丁基、異丁基、第三丁基、苯基,及苯甲基所構成之族群;
其中,R1-R4彼此獨立地係選自由氫、一經取代之烷基基團、一經取代之烷氧基基團.一未經取代之烷基基團、一未經取代之烷氧基基團、一經取代之芳基基團、一經取代之芳氧基基團、一未經取代之芳基基團,及一未經取代之芳氧基基團所構成之族群。
“有機”及“有機性”之用辭於此處使用時係指包含彼此主要係共價鍵結之碳原子及氫原子及選擇性之雜原子(即,非碳或氫之原子)之化合物或部份。較佳之選擇性雜原子包括氧原子及氮原子。“有機”及“有機性”化合物及部份內之雜原子的數量係少於碳原子之數量,且較佳係少於碳原子數量之一半。
“烴基”及“亞烴基”之用辭係指包含彼此共價鍵結之碳原子及氫原子之化學結構或部份。在雜原子不會對此等部份增加顯著反應官能性之範圍內,此等結構或部份可除碳及氫外另外含有其它原子或含有非碳及氫之原子(此處稱為“雜”原子)。此等可接受雜原子之例子係醚氧或硫或硫醚硫原子。此等部份較佳係不含有任何雜原子。
“wt百分率”之表示意指“重量百分率”。
“-OMe”之表示表示一甲氧基基團。
本發明之含磷產物可自組份(A)與組份(B)間之反應獲得。本發明之產物於其化學結構中含有一磷元素,使用可作為用於製備阻燃性材料之原料。於此實施例,此產物可被認為係環氧樹脂之交聯劑、固化劑或硬化劑。
本發明之產物一般係具有至少4重量%且於另一實施例係至少6重量%之磷含量,使其可作為阻燃劑材料。此產物較佳係實質上無溴原子,且更佳係實質上無鹵素原子。
含有機磷之化合物,組份(A),一般係以具如下化學式(I)之結構之化學式表示:
磷原子可與二個別之有機部份鍵結,或可與一有機部份鍵結。當與一有機部份鍵結時,此等鍵可與此有機部份之相同原子連接形成一雙鍵,或較佳地,可為將磷原子與相同有機部份之不同原子連接之單鍵。
“RA”及“RB”可為相同或不同,且係選自經取代或未經取代之芳基或芳氧基基團、經取代或未經取代之烷基或烷氧基基團,且“RC”係具有1至12個碳之一烴基基團,諸如,甲基、乙基、異丙基、正丁基、異丁基、第三丁基、苯基,或苯甲基。“RA”及“RB”可被組合產生諸如以新戊二醇、乙二醇或兒茶酚為主之結構之環狀結構。
於一實施例,含有機磷之化合物,組份(A),係相對應於下列化學式(III)至(V)之一:
化學式(V)係9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物-甲氧基(亦稱為“DOP-OMe”)。
含有機磷之化合物,組份(A),較佳係實質上無溴原子,更佳係實質上無鹵素原子。
組份(A)可藉由任何適合方法合成。有機亞磷酸酯、亞膦酸酯,及次磷酸鹽(個別係具有3、2或1個氧-磷鍵之三價磷化合物)可藉由於鹼存在中將相對應之磷三鹵化物、烷基磷二鹵化物,及二烷基磷鹵化物與醇反應而獲得。
於一實施例,組份(A)係藉由下列方法而製造:起始材料DOP-Cl係藉由於氯化鋅催化劑存在中將鄰-苯基酚與三氯化磷反應而獲得。實驗程序係描述於美國專利申請案第20070173659A1號案。
如美國專利申請案公開第20070173659A1號案中所述,DOP-Cl已知係於酸受體存在中與醇反應產生DOP-Ome。
DOP-Cl係與甲醇反應形成DOP-Ome。此係藉由下列流程例示:
於另外實施例,組份(A)係以下列化學式(VII)-(IX)表示:
組份(B)一般係以化學式(X)表示:
其中,R1-R4係、一經取代或未經取代之烷基或烷氧基基團、一經取代或未經取代之芳基或芳氧基基團。R1-R4可為相同或不同而形成產物。
組份(A)係以下列化學式(XI)-(XIV)表示:
經羥甲基取代之酚及多官能性之酚係已知產物。以鹼催化之酚甲醛樹脂亦已知為可溶酚醛樹脂,係藉由酚與甲醛反應而製造。例子係描述於US 2 912 395、EP 1 352 888 A1及US 2003/0022109 A1。單體、寡聚物或聚合物之酚-甲醛樹脂可使用此等方法合成。一例子於下顯示係用於單體。
製造化合物I之反應包含典型之米歇爾-阿爾布佐夫(Michaelis-Arbuzov)反應,其中,典型上,烷基鹵化物係與亞磷酸鹽反應以便形成相對應之膦酸鹽、亞膦酸鹽及膦氧化物(Pure Appl.Chem.9:307-353;Chem.Rev.81:415-430)。
對於米歇爾-阿爾布佐夫反應非典型係包含醇。於本發明,吾等發現DOP-Cl可與苯甲醇反應進行阿爾布佐夫重排反應產生P-C鍵。
為製備化合物(I),組份(A)係與組份(B)於一反應容器內混合,且混合物於較佳係低於起始材料之分解溫度的溫度之高溫加熱。反應混合物於60-220℃加熱,較佳係最高達100-200℃,且更佳係於150-200℃。
本發明之反應較佳係於無水存在下實行(一般水係以少於5重量%存在,更佳係少於3重量%,且最佳係少於1重量%),因此,水會易於與組份(A)反應。醇係以反應副產物形成。若欲移除醇,反應容器內之厚度可降至低於大氣壓之壓力,諸如,12-300 mm之壓力。反應容器可選擇性地以氣體或揮發性有機液體沖淨,以進一步助於移除副產物。氣體或揮發性有機液體較佳係對於反應容器內容物係呈惰性。
組份(B)可以固體使用,或可溶於熟習此項技藝者所知之有機溶劑,諸如,二甲苯、環己酮、Dowanol PMA或Dowanol PM(陶氏化學公司之商標);於添加組份(A)前,部份溶劑可藉由熱或對溶液施加真空而移除。組份(A)及組份(B)注入反應混合物內之順序並不重要。
以起始組份B之總羥甲基官能性為基準,組份(A)及(B)
較佳係以範圍1:1至4:1之化學計量比率混合。
獲得之產物係具可接受之純度。進一步純化可藉由將產物溶於諸如氯仿或甲苯之溶劑內及添加二乙基醚將產物沉澱而進行。最終產物可於溫度不超過100℃之真空爐或對流爐內乾燥。反應較佳係進行足以將組份(A)之P-ORC部份與組份(B)之OH部份反應之時間。反應時間典型上係從30分鐘至5小時,較佳係從1小時至3小時,且更佳係從2小時至3小時。
若要的話,諸如催化劑或溶劑之其它材料可添加至組份(A)及(B)之反應混合物。
自組份(A)與組份(B)間反應而形成之本發明含磷產物(化合物I)具有較佳係至少約4重量%且更佳係至少約6重量%之磷含量,以使其可作為阻燃劑材料。產物較佳係實質上無溴原子,且更佳係實質上無鹵素原子。一般,自組份(A)與(B)反應而形成之產物可為一或多種不同寡聚物之摻合物。
於另外實施例,產物可以下列化學式(XV)表示:
其中,R1-R4係氫、一經取代或未經取代之烷基或烷氧基基團、一經取代或未經取代之芳基或芳氧基基團。
R1-R4可為相同或不同而形成產物。
“RA”及“RB”可為相同或不同,且係選自經取代或未經取代之芳基或芳氧基基團、經取代或未經取代之烷基或烷氧基基團。“RA”及“RB”可組合產生諸如以新戊二醇、乙二醇或兒茶酚為主之結構之環狀結構。範例係以下列之化學式(XVI)至(XXIII)提供:
化合物(I)之應用係描述於WO 2005/118604 A1。
於本發明之一實施例,如上所述可藉由將組份(A)與組份(B)反應而獲得之含磷產物可作為一可固化(可交聯)含磷阻燃環氧樹脂組成物之一組份。
本發明之組成物可用以藉由產業所知之技術製造複合材料,諸如,藉由拉擠成型、模製、包覆,或塗覆。本發明係特別有用於藉由產業已知技術製造黏著劑、塗覆物、
複合物、鑄件、嵌裝材料、B-階段預漬體、層合物、結合片材,及經樹脂塗覆之銅箔。
下列範例係意欲例示本發明及教示熟習此項技藝者製造及使用本發明。此等範例非意欲以任何方式限制本發明。
於1公升反應器內,於氮氣下,23.5克(0.1莫耳)之DOP-Cl及10.1克(0.1莫耳)之三乙基胺添加至100毫升之攪拌甲苯。混合物使用冰/鹽浴冷卻。3.2克用量(0.1莫耳)之甲醇經由添加漏斗緩慢添加,使反應溫度保持於0-10℃。甲醇添加完全後,冷卻浴以一加熱罩替換,且反應混合物加熱至50℃,且持續攪拌另外3小時。然後,移除加熱罩,且使反應混合物冷卻至室溫。三乙基胺氫氯酸鹽被過濾,且濾液於使浴溫度保持低於100℃之完全真空下使用旋轉式蒸發器濃縮。DOP-OMe之粗製產率:90%,淡黃色油。產物可於未進一步純化而用於下步驟。
110.5克用量(0.48莫耳)之DOP-OMe及34.7克(0.1莫耳)之四甲基醇Bis-A稱重至一500毫升之一頸RB燒瓶。然後,混合物附接至具有一接收燒瓶之Kugelrohr裝置。此等燒瓶藉由使用真空泵施加200mm直空而緊固。加熱腔室加熱至100℃,且於此溫度保持30分鐘,此時,甲醇開始冷凝於接收燒瓶內。然後,反應混合物於30分鐘期間緩慢加熱至170℃,且於此溫度保持另外30分鐘。然後,停止加熱,且
形成之固體冷卻至室溫。然後,移除反應燒瓶,且添加200毫升氯仿以溶解固體產物。溶液被轉移至一Erlenmeyer燒瓶。攪拌時,添加100毫升之二乙基醚。沉澱之白色固體使用真空吸濾,且於50℃之真空爐內乾燥。粗製產量:101克之t-mDOP Bis-A。
對照組成物
一比較物係使用含有XZ-92741(可得自陶氏化學公司之一商業上硬化劑)之一無鹵素之磷官能化之對照組成物製造。組成物中使用之組份係於下表中提供。
此比較物係藉由以t-mDOP Bis-A替換XZ-92741而製造。清漆之製備係使用下列程序完成。
1.使用二甲基甲醯胺作為溶劑製備10重量DICY溶液
2.使用DOWANOLTM PM作為溶劑製備2-苯基咪唑(2-PI)之20重量%溶液
3.添加DICY及2-PI溶液(2-PI)至XZ 92741.00硬化劑且
攪拌至獲得一均質溶液為止。
4.添加DENTM 438環氧樹脂溶液
撫熟反應性係使用IPC-TM-650 No.2.3.17決定。計時器係於一旦1.5毫升之清漆被置於171℃之熱板上開始。於以一木製壓舌板操作前,清漆係留置於熱板上1分鐘,以便蒸發殘餘溶劑。清漆被操作及混合,且決定材料於自熱板表面升高時不能形成線狀物時之膠凝。總時間被記錄為撫熟反應性或凝膠時間。
然後,經膠凝之樹脂被收集且置於190-200℃之爐內後固化1.5小時。小片之經後固化的樹脂被置於一熱重量分析器(TGA Q50 or 2050,TA Instruments)獲得分解溫度,Td,其係定義為樣品5%重量損失發生時之溫度。TGA測量係於氮氛圍下以10°/分鐘之加熱速率進行。樹脂亦使用差式掃瞄熱量計(DSC Q1000,TA Instruments)分析測量組成物之玻璃轉化溫度,Tg。使用方法係IPC TM-650 2.4.25。
比較係於含有XZ-92741(一種專賣之含磷環氧樹脂)之
一組成物與其中XZ-92741係以t-mDOP Bis-A取代之一組成物間進行。此組成物係以相同重量%之P填充量進行。
本發明範例組成物係顯示於下之第I表。
對照組及本發明範例之Tg值係顯示於下之第II表。
數據顯示t-mDOP Bis-A組成物顯示改良之Tg。
Claims (14)
- 一種用於製造含磷化合物之方法,包含將(A)與(B)接觸,其中(A)係以下列化學式界定:(A)
- 如申請專利範圍第1項之方法,其中,該化合物(B)係以下列化學式界定:
- 如申請專利範圍第1項之方法,其中,該化合物(B)係以下列化學式界定:
- 如申請專利範圍第1項之方法,其中,該化合物(B)係以下列化學式界定:
- 一種用於製造可固化含磷環氧樹脂組成物之方法,包含:摻合(I)一含磷化合物,其包含下列之反應產物:(A),其係以下列化學式界定:
- 一種含磷化合物,其係藉由包含將(A)與(B)接觸之方法製備:
- 一種清漆,其係自申請專利範圍第5項之組成物製造。
- 一種預漬體,其係自申請專利範圍第7項之清漆製備。
- 一種電層合物,其係自申請專利範圍第7項之清漆製備。
- 一種印刷電路板,其係自申請專利範圍第7項之清漆製備。
- 一種塗覆物,其係自申請專利範圍第5項之組成物製備。
- 一種複合物,其係自申請專利範圍第5項之組成物製備。
- 一種鑄件,其係自申請專利範圍第5項之組成物製備。
- 一種黏著劑,其係自申請專利範圍第5項之組成物製備。
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US201161489705P | 2011-05-25 | 2011-05-25 |
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US (2) | US9388297B2 (zh) |
EP (1) | EP2714702A2 (zh) |
JP (1) | JP6124876B2 (zh) |
KR (1) | KR20140024000A (zh) |
CN (1) | CN103547586A (zh) |
SG (1) | SG194859A1 (zh) |
TW (1) | TWI572614B (zh) |
WO (1) | WO2012161926A2 (zh) |
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CN104747373A (zh) | 2013-12-31 | 2015-07-01 | 通用电气公司 | 用于保护风力涡轮机电池备用变桨控制系统的系统和方法 |
CN107266639B (zh) * | 2014-08-15 | 2019-08-27 | 江苏雅克科技股份有限公司 | 含磷酚醛树脂化合物及以其为原料制备的含磷阻燃环氧树脂固化物 |
JP6519768B2 (ja) * | 2014-11-12 | 2019-05-29 | Dic株式会社 | 難燃性樹脂組成物、成形体およびそれらの製造方法 |
CN107206119B (zh) | 2014-12-09 | 2021-01-29 | 实体科学公司 | 具有生物相容性层的医疗设备涂层 |
US9845765B2 (en) | 2015-01-12 | 2017-12-19 | General Electric Company | Piston assembly for a reciprocating engine |
US10723747B2 (en) * | 2015-09-29 | 2020-07-28 | Nan Ya Plastics Corporation | Low DK phosphorous containing hardener useful for halogen free, flame retardant polymers and use |
TWI671355B (zh) | 2018-01-03 | 2019-09-11 | Taiwan Union Technology Corporation | 樹脂組合物,以及使用該組合物所製得之預浸漬片、金屬箔積層板、與印刷電路板 |
TWI668228B (zh) * | 2018-05-21 | 2019-08-11 | 國立中興大學 | 磷系化合物、其製備方法與阻燃固化物 |
CN110655536B (zh) * | 2018-06-28 | 2022-03-01 | 台光电子材料(昆山)有限公司 | 一种含磷化合物、含磷阻燃剂及其制备方法与制品 |
CN111849270B (zh) * | 2020-07-29 | 2021-12-10 | 陕西科技大学 | 一种氮磷硅协同煤炭阻燃抑尘剂及其制备方法 |
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- 2012-05-01 SG SG2013082953A patent/SG194859A1/en unknown
- 2012-05-01 US US14/110,939 patent/US9388297B2/en not_active Expired - Fee Related
- 2012-05-01 KR KR1020137030733A patent/KR20140024000A/ko not_active Application Discontinuation
- 2012-05-01 CN CN201280024908.5A patent/CN103547586A/zh active Pending
- 2012-05-01 JP JP2014512850A patent/JP6124876B2/ja active Active
- 2012-05-01 WO PCT/US2012/035933 patent/WO2012161926A2/en active Application Filing
- 2012-05-01 EP EP12721085.4A patent/EP2714702A2/en not_active Withdrawn
- 2012-05-24 TW TW101118525A patent/TWI572614B/zh not_active IP Right Cessation
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US20140249253A1 (en) | 2014-09-04 |
US20160319107A1 (en) | 2016-11-03 |
TW201247692A (en) | 2012-12-01 |
KR20140024000A (ko) | 2014-02-27 |
WO2012161926A2 (en) | 2012-11-29 |
US9388297B2 (en) | 2016-07-12 |
JP6124876B2 (ja) | 2017-05-10 |
EP2714702A2 (en) | 2014-04-09 |
JP2014516973A (ja) | 2014-07-17 |
CN103547586A (zh) | 2014-01-29 |
US9752010B2 (en) | 2017-09-05 |
SG194859A1 (en) | 2013-12-30 |
WO2012161926A3 (en) | 2013-01-17 |
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